Family-friendly vacation rentals in Grassina
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Top-rated family-friendly rentals in Grassina
Guests agree: these family-friendly homes are highly rated for location, cleanliness, and more.
Vacation rentals for every style
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Popular amenities for Grassina family-friendly rentals
Family-friendly home rentals with a hot tub
Home in Gaiole In Chianti
4.86 out of 5 average rating, 248 reviewsCharming estate with views
We loved Bernardino's place. It was super cozy, the garden and whirlpool were amazing. The kitchen had everything we needed. And Bernardino was super helpful with tips and answers to all our questions. Highly recommend if you're looking for a remote place to enjoy Tuscany.
Farm stay in Greve in Chianti
4.99 out of 5 average rating, 172 reviewsAncient Casolare Toscano on the Chianti hills
Giovanni's property exceeded our expectations in every way! From the warm welcome with a delicious charcuterie board and homemade wine to the exceptional hospitality throughout our stay. Giovanni was an outstanding host, providing invaluable suggestions and insider tips for exploring the area. Highly recommend Giovanni's property for its stunning beauty, warm hospitality, and unique experiences. We wished we had booked more nights to fully enjoy the property's amenities, including the olive pressing experience, which unfortunately we ran out of time.
Apartment in Centro Storico
4.93 out of 5 average rating, 279 reviewsM&G Apartment your home away from home
Massimiliano was gracious and friendly. The location is great for those willing and able to walk 15-30 minutes as that will get you to countless trattorias, cafes, and museums. If you are visiting from a city, this apt will feel like home. If you are from a quiet suburb or town, be aware that weekend nights will be filled with people in the streets until the wee hours. We would gladly stay here again.
Villa in San Casciano in Val di Pesa
4.94 out of 5 average rating, 160 reviewsThe Vichiaccio Villa with Jacuzzi in Chianti
A lovely home that has clearly been well cared for alongside a beautiful landscape of vineyards and olive groves. Our host was very attentive and available for any questions and we couldn't have had a nicer time.
Apartment in Gavinana
4.96 out of 5 average rating, 391 reviewsSuite Michelangelo with Terrace
Spacious apartment, great kitchen, big bathroom and lovely balcony overlooking Florence. Luciano is a very nice and helpful host. The parking space we parked the car on as it was not needed during the stay. Instead we got the bus that stopped close to the apartment. We appreciated that there was coffee, cookies and other edible in the kitchen and that we didn't have to buy dish soap, toilet paper, paper towels, soap and shampoo. Thank you Luciano for your hospitality! We would be glad to come back!
Condo in Centro Storico
4.9 out of 5 average rating, 100 reviewsFortress area, Mansarda with terrace, Jacuzzi, A/C
We had a great time staying here! Very clean, cosy and comfortable, with lots of space and a lovely jet bath which was perfect for relaxing after the Firenze Marathon!
Farm stay in Figline Incisa Valdarno
4.94 out of 5 average rating, 344 reviewsRomantic in bioagriturismo Florence
The room was very spacious, comfortable and quiet. Francesca was very welcoming. The breakfast basket was a delicacy that you cannot miss. We also found a lot of wild animals nearby. People who like animals and quietness must not miss it. And we only found out that we forgot to leave the room key after we left. Later we drove back to return the key. I apologize to Francesca again for causing you unnecessary trouble.
Loft in Centro Storico
4.96 out of 5 average rating, 422 reviewsLittle Jewel Florence , Dome, David, - Garage
This room receives the morning sun. Surrounded by antique furniture, you will feel like you are living here. Once you step out of the building, you can enjoy the wonderful view of the Duomo. Riccardo has taken care of me in many ways.Thank you,Riccardo!
Family- and pet-friendly home rentals
Home in Radda In Chianti
4.84 out of 5 average rating, 173 reviewsTuscany House "La Querce Sola"
Beautiful home with a gorgeous view of the Tuscan hills! Peaceful but still accessible to everything in area within an hour drive. We were definitely glad to have an SUV as our rental car, as the dirt road into the property is very bumpy. Rosanna was super friendly and accommodating - would definitely recommend staying here!
Guest suite in Centro Storico
4.95 out of 5 average rating, 164 reviewsA stone's throw from downtown and away from the chaos
I had a great time exploring Florence — and Italy as a whole — for the first time, and felt right at home thanks to Ms Stefania. Meeting her family and staying under their wing is a memory of its own. We maintained contact throughout my stay, with Ms Stefania checking in on me and ensuring my satisfaction. I even had the pleasure of meeting her pets up close and personal! The neighborhood was an eye candy with its picturesque buildings and narrow streets. As a solo female traveler, I felt as safe walking alone at night as I do at my own home. I couldn’t recommend Ms Stefania’s home enough and look forward to booking again in the future!
Home in Borgo San Lorenzo
4.82 out of 5 average rating, 303 reviewsMugello Countryside House
Me and my wife had a wonderful stay at Lucrezia’s place, which offers a perfect blend of country charm just outside Florence. It’s conveniently located for a quick drive or train into the city whenever needed. The accommodations are both relaxing and comfortable, with everything you need to prepare meals at home. Lucrezia also recommended a fantastic local restaurant that exceeded my expectations. The property’s location is ideal, and I definatly recommend it to anyone looking for a peaceful getaway!
Home in Rifredi
4.87 out of 5 average rating, 128 reviewsFrom Chiara - Your City Countryside
Aldo was a lovely host! He came to the airport to pick us up and take us to the flat. The flat is in an olive grove and the harvest was under way when we were there. Aldo gave us a bottle of the their freshly pressed olive oil. Delicious!
Home in Centro Storico
4.85 out of 5 average rating, 439 reviewsSan Gallo Suite in Florence Center
My gf and I loved Agnese’s apartment. Everything was within walking distance and yet felt far away enough from all the crowds and noise. This was the largest airbnb we stayed at throughout our trip by far so that was nice to have all the space! And we also had a cab scheduled by Agnese on our check out date. She was very responsive and kind and I would stay here again next time I come visit.
Vacation home in Panzano In Chianti
4.97 out of 5 average rating, 141 reviewsFienile Santa Teresa
Very private and peaceful. Beautiful view and the house was well equipped and comfortable. Host was very responsive and helpful.
Condo in Castelfranco di Sopra
4.83 out of 5 average rating, 232 reviewsHouse between Firenze, Arezzo, chianti e Siena
Splendid location and excellent food! Perfect getaway in my opinion — I saw the prettiest sunset of my life surrounded by cats and ducks.
Apartment in Scandicci
4.86 out of 5 average rating, 140 reviewsCasa Gina - Welcome in Italy! Happy June 20% off
We had a great stay in Davide’s place. Easy to reach Florence by tram and very nice neighborhood.
Family-friendly home rentals with a pool
Villa in Panzano In Chianti
4.93 out of 5 average rating, 70 reviewsLuxury Villa on Chianti Wine Estate
Our stay at the villa felt like living in a postcard- breathtaking surroundings! The historic villa was charming and comfortable for our group of 5. The area is idyllic and the onsite winery is a fantastic plus. We enjoyed the fireplace and the outdoor areas. Great laundry facilities as well . Vicky was very helpful and gave us great advice on local sites. We would definitely return !
Apartment in Gaiole In Chianti
4.76 out of 5 average rating, 21 reviewsIdyllic with shared pool in the heart of Chianti
Heidi's apartment is situated in a larger complex on the outskirts of the village, just a short walk from the town center where you can find a church, a mini supermarket, bars, and a popular restaurant that is always fully booked. The village is ideally located in the heart of Chianti, making it a perfect starting point for exploring the region. You can drive along one of the scenic, winding roads to a wine tasting event, enjoy a bike ride through the picturesque countryside, or visit nearby cities like Siena or Florence (Firenze). One of the highlights of the apartment is the spacious swimming pool (1.35 m deep), which is perfect for cooling off during the hot summer days, especially if you have kids. The apartment itself is well-equipped, ensuring a comfortable stay. Communication with Heidi is easy and friendly. She provides detailed information on the check-in and check-out procedures, as well as instructions for using various amenities in the complex. We enjoyed our stay!
Farm stay in Reggello
4.87 out of 5 average rating, 127 reviewsHoliday accommodation in Tuscany
Ewa was such a friendly host. She worked with us, despite us having some changes in our arrival plan. The place was clean and the kitchen was very well-stocked with pots, plates, pans, utensils, which was useful for us as a vegetarian family with allergies. My family had never had an agriturismo experience, and Ewa made it an amazing one. Tip: try her amazing olive oil and pick some up before you leave!
Hut in Poggibonsi
4.94 out of 5 average rating, 129 reviewsLovely barn with pool between Siena and Florence
Great stay here during our time in Tuscany. The roads can be as you approach Michele's place so definitely recommend a small suv or something like that. Michele's was very friendly and flexible on things and even brought us a few things to do laundry with. There are two sweet cats that live on the property and one will come and greet you every morning if you're nice to it. We stayed here while spending time in Florence, Siena and the town of Poggibonsi is about 15 minutes away if you need groceries or a close dinner.
Apartment in La Felce
4.98 out of 5 average rating, 107 reviewsLa Felce Country House
Cristina is the ultimate host! Everything was immaculate and set up for us. We traveled with two young kids, and she was proactively prepared with a crib & high chair. She also had amazing recommendations and answered any questions for us. Led us to a spectacular sunset winery in the hills. The premise has stunning views and hanging poolside in the mountains, was just what the doctor ordered. Highly recommended and makes you feel like family!
Farm stay in Passo dei Pecorai
4.94 out of 5 average rating, 70 reviewsCharming Cottage among vineyards with private pool
I loved our stay at this beautiful Tuscan villa! We had such a wonderful experience and Olivia was SO helpful! The grounds are gorgeous, the wine was amazing. My only regret was not staying longer than three days! I hope to return to Casavecchia de Nozzole again!
Villa in Certaldo (FI)
4.89 out of 5 average rating, 143 reviewsTuscan farmhouse with private pool and views
Fantastic accommodation with lovely views of the countryside. Especially loved the fire place and large spacious kitchen. Charley and Ann were very gracious hosts and I would have no problem recommending this accommodation to anyone who wants to visit Tuscany. The accommodation was within 30 mins of most tourist towns and trains which made it excellent for day trips.
Home in Firenze
4.89 out of 5 average rating, 152 reviewsIl Melograno, Florence hills & pool & olive oil
We had a great stay. Great spot for families, close enough to Florence to walk but far enough away to relax. We even had the opportunity to help pick olives. The kids loved the tree house and trampoline.
Quick stats about vacation rentals that are family-friendly in Grassina
Total rentals
30 properties
Nightly prices starting at
$100 before taxes and fees
Total number of reviews
590 reviews
Rentals with a pool
30 properties have a pool
Wifi availability
30 properties include access to wifi
Popular amenities
Kitchen, Wifi, and Pool
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